Going Darkside
by Redwinged Blackbird
Summary: Sam is going to rescue Dean from hell no matter what the cost... Much ANGST! And of course Dean in hell... Hurt Dean. Now Updated.
1. Chapter 1

**Disclaimer: I don't own Sam, the car, Bobby, or the Colt--I'm more a fan of stabbing so it's Ruby's knife I want.**

He had it. Sam had a plan. A half assed planned one, but still a plan.

It felt awkward driving Dean's car. It was just torture when his music immediately came on. And Sam almost lost it when he had to repair Dean's car at Bobby's.

There was no 'one working part' this time. It was nearly hopeless. Even to Sam.

"You know you're welcome to stay as long as you need to Sam."

"No." Sam was cold and looked away. He offered Bobby a smile, "Thanks though."

"I don't think it's a good idea for you to be picking up hunts."

"Who said anything about hunting?"

"What the hell?! You're not thinkin' about goin' after Lilith!"

"No."

"Well... call me. Stay safe and don't turn wreckles like-" Bobby cut himself off. "Stay safe."

"I've gotta run."

Sam got in the car and opened the glove box. He put a devil's trap on it and inside was the colt. No one was getting to it. Sam was going to drive non-stop. Dean-or Dean's body was in a safe place. Sam convinced himself that Dean could turn into a demon. He had the tatoo... and if that didn't work Sam was getting Dean out before Dean could even blink and have his eyes turn dark.

Sam finally made it and he stood in the cemetary staring ahead. He knew what was behind the gates. Demons, everything nasty that wanted Sam dead, not to mention hell itself, but Dean was in there too.

Sam sighed holding the colt. "If Dad could climb out, so can you Dean..." Sam paused, "God knows if you don't I'll dig you out myself." He had Ruby's knife tucked in his jeans. Today's forcast: Overcast with a chance of the Doors of Hell breaking open and demon possetion.

Sam put the colt into the slot like Jake did a year ago and Sam waited.

Nothing happened.

"What the hell?" Sam looked at the doors after a minute and pulled out the colt.

Still nothing.

Then Sam realized... When they repaired the colt, they neglected the fact it used to be a key...

The key didn't fit. The gun worked, but the key didn't.

Sam threw the colt down and pushed and banged on the doors to open. There's no chance of budging them.

"DAMNIT" Sam sunk to his knees. "C'mon...DEAN!!" Sam wished Dean could hear him somehow.

"Fine. Navigator goes down with the ship too." Sam picked the gun up again, held it, put it to hit head and cocked it.

He closed his eyes...

A gunshot rang out from the cemetary...

A woman stood above Sam. "Oh Sammy, I'm surprised at you. Well, not really."

_**TO BE CONTINUED...**_

**AN: This is something I have on the side. If it goes over well then YAY! But if not then don't expect much. You know where the button is. Tell me what you think.**


	2. Chapter 2

**Disclaimer: Although my life may be hell sometimes, I have no access to Sam, Dean, or the pretty car :'(**

**Many thanks to the lovely reception. You've moved me to write sooner... So this was written in about 30 min :D**

"NOOO!! SAM!!" Dean was crying out for him suspended by meat hooks. He really was in hell. Dean could tell it had been days now, but they felt like years, since he died.

"Hello Dean." A demon passed by. "Remember me?" She punched him and kicked at him.

"AHH! Damnit. Leave me alone you ugly son of a bitch!"

"Well... I remember you." It smiled with black eyes. "You and _Sammy._"

"Shut the hell up!"

"Aww... poor Dean. It looks like you'll never see your dear little again." It teased.

"Shut up bitch or so help me-"

It laughed. "Send me to hell?" It stroked Dean's cheek and he grimaced. "Baby you already did. And guess what? Looks like I was right when I promised to see you in hell."

"I think I said that right before the exorcism in the prison. But hey, not like it matters, here you are." Dean smiled at it until another hook dug into his side and he screamed.

"Ya know Dean, Sam's not doin' so great right now."

"DON'T YOU DARE TALK ABOUT MY BROTHER!!" He tried to get at her but the meat hooks made it impossible.

"Yeah." It ignored him and circled him. "Sammy's still up there in the land of the living."

"Aghh you bitch! Just shut up."

"But you wanna hear something?" It got closer.

"Not from you!"

"Well I'll tell you anyway..." It got closer to his ear. "Sam's in bad shape. He's cold. Sammy doesn't care about anything anymore. _Cold."_

"No, Sam's not like that." A hook twisted in his shoulder.

"Turns out he is." It smiled. "And do you know where he is right now?"

"Just go away bitch."

"I have a name!" It forgot the torture she was putting Dean through at the moment.

"I don't give a shit about your name or what you have to say!"

"Well... Sammy's upstairs with the colt right now."

Dean's eyes widened. He shouldn't listen. "Demons lie!"

"Like you were all honest! You'll be one of us soon."

"I'd-"

"Burn in hell before you do?"

"Just go away." Dean muttered.

"Ok, Sammy. Where was I...?" She pondered. "Oh yeah, the colt. We'll he's in a cemetary and you know where..." It smiled. "Right know he's just standing there, knocking on the door..."

"You LIE!"

"He's gonna open it... all for you..." It got in his face. "It's gonna be pretty hard for you to get out with all those lovely hooks when it does open."

"He wouldn't."

"He would and is... I'll let you hear him..."

Dean listened and heard Sam's voice. "Sam! SAMMY!"

"He can't hear you and if you keep this up you'll miss what he's saying to his dearly departed Dean."

_"...climb out... if you don't I'll dig you out myself..."_

"And I'll be out with a whole lot of others to great him. And if it doesn't open... you're his brother. You know what he'll do... with that_ gun..._" She turned her back and left.

"NOO!! SAM!!"

**AN: I had a totally different chapter two written, but it'll work better as a third chapter. Cliffy... yeah, I'm a mean author with this one :D. So yay for all of you that get a kick out of this flavor of angst.**

**Press the button for free brownies. :D**


	3. Chapter 3

**Thank you to my reviewers.**

**Disclaimer: I'm broke and can only afford duck tape and ramen. yes, duck tape.**

The woman looked down on Sam and shook her head with her hands on her hips. "I thought you were a lot smarter-better than this." She looked up and scoffed. "It's more than a little bit pathetic, don't you think?" She looked back down at Sam on the ground. "Oh come one. You're not dead yet. Quit starting into space and get up." She offered a hand.

"H-how? I mean what...?" Sam looked around and ran his hand through his hair.

"Couldn't let you just waste yourself Sammy." He was still confused. "Gun's over there Sam." She pointed to the smoking gun across the cemetary.

"How am I not dead? Unless..." It hit him like a wall. "You're a demon." He took a step back and took out the knife.

"Bingo, but not quite the reception I wanted. Kinda saved your ass. _Again."_

"Who the hell are you!?" He held the knife closer.

"Jesus you're dense today." She cocked her head and blinked. "Take a guess."

Sam looked at the woman. Brown hair pulled back into a pony tail, not really tall or short. But the same body posture and carriage as...

"...Ruby?"

"We have a winner." Ruby had already picked the colt back up and offered it to Sam. "I'd like my knife back."

Sam looked at her and made the exchange.

"How...?"

"Oh Lilith? Please, she can do a lot of fancy tricks, but she couldn't send me back there..." Ruby looked at the door.

"Where'd you go then?"

"Oh. Just got kicked out of that body--which I kinda liked--got sent half way around the world, smacked face first into a gate and she neglected to notice that it wasn't open. And then I came all the way back here to find you trying to go into the pit."

"And."

"And? Not the best idea Sam! What did you think would happen?"

"I don't know, but Dean's on the other side! I don't give a crap."

"So... You have the idea that Dean would spring out like magic." Ruby nodded her head. "You want to know what would've happened?"

"What."

"Picture unleashing more Demons. Some _might_ follow you, but you're the under dog so I think most of them are banking on Lilith."

"Last time I saw her she ran off."

"It's called re-grouping Sam, do you even know where she is?"

"Do you?" Sam threw it back.

"No. But it can't be good Sam."

Sam looked back at the door and studied it. "I don't care. My priority list is slightly different and I'm not stupid enough to go in without a plan."

"You call what you just did a _plan_? You almost blew your brains out with the _Colt_."

Sam looked at the gun and back at Ruby. "It would've worked Ruby."

"Yeah, and then some. Think about it. That gun... will not only kill you. It destroys you. EVERYTHING about you would've died."

Sam suddenly felt stupid. "What do you suggest then?" Sam looked her in the eye. "What's your...Brilliant...'plan'."

"First, do the world a favor. Don't blow your brains out. Second, you're going to trust me and listen to everything I say."

"Why should I? Demons lie."

"So do you! And you'll do it if you want Dean back."

Sam paused.

"Come on Sam. You don't exactly have the best track record when you don't take my hints..."

"It'll bring Dean back?"

"It's the only shot you have."

Sam stood and thought... _What would Dean do? What did Dean always do? But Dean's not exactly here..._

**AN: CLIFFY :D muhahahaha. Hey, I didn't kill Sam off. (although I thought about it.) You know where the button is.**


	4. Chapter 4

**It is 1:30 AM where I am. Forgive mistakes and I'm updating so please review. It is very hard to type after burning your hands with a hot glue gun!**

**DISCLAIMER: I don't even own Mr. EVIL Hot Glue Gun.**

Dean watched all the demons making a rush to the door. He couldn't get free no matter how hard he tried. There were usually screams, but it suddenly got quiet. They were waiting.

He didn't know what was worse, the eerie silence in hell, or the riot that followed when the doors failed to open. Part of Dean sighed in relief, but then he remembered the demon's words about what Sam would do with the gun if it didn't work. Images haunted him and he was screaming his brother's name hoping that some how he could save Sam.

"...Wow Deano." Another demon decided to pay a visit. "Looks like your brother really is a failure. Can't be a leader, can't even save his brother."

"He never wanted to lead you!"

"I wonder what's going on upstairs... What is Sammy doing now that his plan's ruined?"

The images came back and Dean tried to will them away. "Screw you." Another meat hook latched on catching Dean off guard making him throw his head back and scream.

"You know what... because I'm so nice... I can tell you how to get out of those hooks and avoid getting another piercing..."

Dean. Wanted. Out. "How?"

"Give in Dean..."

"What?!"

"You're still holding on to humanity... become one of us..."

"Never!"

"It's not all bad Dean. You'll forget about everything before this if you do. No more hooks."

"Don't want to forget. I'll never be like you!"

"Aww... Come on. All the cool kids are doing it." The demon laughed. "You can possess people, you won't die, and the general demon package that goes with it."

"I sold my soul. Not my humanity. You sold your dignaty, your soul, and your humanity. Demons are lower than slime. So get your disgusting face away from me!" Another meat hook.

"Not nice Dean. I think I forgot to mention that everytime you badmouth a real demon down here, the worse it gets. So I'd consider my options if I were you."

Dean kept his mout shut.

"Good." The demon punched Dean in the face. "You might actually be learning."

Blood poured from Dean's nose and mouth. He had a dazed look.

"Now what do you say when one of us pays a visit?"

"Screw you." A meat hook tugged on Dean harder.

"Try again."

Dean didn't say anything and the demon slapped him. "You're going to learn to treat us with respect and the pecking order down here!"

He tried to mask the pain.

"I'll make sure you get extra special attention. Expect some visits from higher ups." It started to pass him. "Only the best for a Winchester." It mocked.

Dean knew three things. If his dad could make it for a year, so could he. He had to find out about Sam. And he could absolutely NOT give in. And so started his mantra..._ Dad could do it, so can I... Save Sam... Don't let them win..._ but a tiny voice would chime in now and again..._ You can make the pain stop..._ Dean told the voice to go away and ignored it._ Just let go..._

"...We have cookies."

Dean's head snapped up to another demon laughing in his face. He shot daggers at it and it earned him a beating.

"You DO NOT get to make eye contact with me Winchester. Only when I say."

Dean looked up again earning him a tug on the meat hooks. But he still kept eye contact.

"You have a lot to learn about hell..." It made a spark of lightning hit the meat hooks. Dean's body jolted with the surge of electricity.

Not that Dean was giving in... but he looked down, he was just sooo tired... or was he? His body and mind didn't know the difference and the demon was satisfied.

"Good boy." It patted Dean like he was a dog.

"...Get...y-your hands. Off of m-me..." Dean still had some fight for this demon.

"You're so much like your father Dean. But there's one difference, you're broken on the inside. Not sure about your little brother... your Dad died only for you to find your way down here. You have nothing to hold on to."

_Dad could do it, so can I... Save Sam... Don't let them win..._ _Dad could do it, so can I... Save Sam... Don't let them win..._ _Dad could do it, so can I... Save Sam... Don't let them win..._

_...Let go..._

**AN: Dean's in some trouble now. Will Sam save him before it's too late for Dean? Stay tuned and please review. It is now 2 AM. Humor me please.**


	5. Chapter 5

**DISCLAIMER: I'm living off of tomatoes at the moment. I doubt Kripke would let me have Supernatural in exchange for tomatoes.**

_But Dean's not exactly here..._ And that was the decsion maker for Sam. He needed Dean to be here.

"What do I do..."

"Well Sam. Like I said before, you're not gonna like it."

"I don't care anymore." Sam's eye's were cold again. Dead on the inside.

"Well that's the spirit!" Ruby tried sarcasm. Sam had his work cut out for him. "Come on. We need to get away from here."

Sam mindlessly followed until they pulled up to the nearest cheap motel.

Ruby got out to get the rooms. "Yeah... Two queens."

Sam cringed a little. They got to the room and it never occured to him that as he took his usual spot on the bed furthest from the door, Ruby would be taking the other bed. Dean's bed.

"Salt the doors Sam."

"You won't be able to--"

"Salt the doors unless you want demons breaking in."

Sam did as he was told. "So what's the plan."

"We need to take down Lilith."

"Ok captain obvious."

"Not just that, we need help Sam."

"Ok, I'll call Bobby and--"

"And have two hunters against Lilith and get yourselves killed. Good luck getting the hunting community on your side. I recall at least one person wanting you dead. What was the word used? Oh yeah, Anti-Christ."

"So you're saying I get help from demons."

"Trust me Sam, it's your best shot."

"Even if that didn't go against everything I stand for, how would I do that? I believe there are more demons out there that want me dead than don't."

"True. But like I said. You aren't going to like it Sam."

He sat there in silence. The stained carpet was very interesting.

"Ya know, if you try hard enough you could probably burn a hole through the carpet."

Sam chuckled. Ruby remained serious...

He sighed. "Ok, what do I do?"

"Step up and be a leader Sam. Rally your own troups. Not everyone is siding with Lilith."

"But you said--"

"I said she had numbers Sam. You won't be going for numbers, it's too late for that. You're going for power instead now. Get the more powerful demons on our team and go from there."

"Before or after they kill me."

"They won't."

"How's that?"

"You scared Lilith back there. Her powers didn't work on you. You know why?"

"...No..."

"Because of Dean. You were so focused on one goal. Save Dean. And then after he died, kill Lilith. One goal, you were sharp. Focused. Nothing else mattered."

"So I focus on Dean?"

"No. Right now he makes you weak. Still a target. You want to focus on getting an army. Nothing else."

"If I do then I--"

"We have cookies Sam." Ruby smiled. "It'll bring out the best in you. You'll do things you've never even dreamed of. You're gonna be a rock star Sam, and I'm going to teach you how." Ruby's eyes went black.

_Dean would say no. Dean would send her to hell. __**Dean isn't here...**_

"What do you say to that?"

Sam looked up with the cold look again. "I'm in." Sam knew what he wanted now. And he was going to get it. One step at a time.

"Atta boy." Ruby sat on the bed and kicked off her shoes. "I'll take first watch. You've got a lot to think about and focus on."

Sam laid down on the bed and turned to face the wall with his back to Ruby. Dead, cold, and staring ahead.

Ruby smiled sitting on the bed.

**AN: There you have it, I know it's a tad short. Love it? Hate it? Dean's POV next chapter of course.**


	6. Chapter 6

**DISCLAIMER: Not even in my dreams unfortunately.**

**It's Dean's turn so here it goes. Welcome to hell. Check out time is never.**

Dean stared ahead blankly. Since the last demon had left it was like some one had turned off the lights. He couldn't see a thing. More disturbing was the silence. Dean could feel the hooks dig into him. He could feel the demons moving around him. He could feel himself let out a scream once in a while when the pain became too much.

He gathered that only a few things could be going on. First being that a demon did something to him and that's why he couldn't see or hear. Second, it had nothing to do with a demon really and his brain was trying to cope. And third... he hated to even think of the possibility that he might be giving in. No. He definitely wasn't giving in. Everytime he told himself that another hook materialized, a hook pulled, or he was struck by lightning again. _Oh yeah Dean. Feel the pain._ He actually took comfort in the thought that if the pain wasn't stopping he wasn't giving in.

Everything suddenly came into focus when Dean heard a demon snap it's fingers. He was back in hell. Sight and hearing included. Apparently his first assumption was correct. He just stared ahead at the demon before him.

"What did I teach you about eye contact?" The demon back handed him.

When Dean's gazed didn't shift and he replaced the dazed look with a cocky grin the demon got angry. "We have some special plans for you today. But I think we might have to make some alterations because you aparently you learned nothing."

"Oh I'm so scared." Dean mocked. "Bring it on." _Feel the pain Dean._

The demon looked to the side. "You asked for it Dean." A smile crossed it's face.

Suddenly the chains were moving, both pulling at Dean and hoisting him higher up in the air. It stopped and he looked down. _What the hell? I'm afraid of airplanes not heights... some one messed this one--_ Dean's thoughts were cut off when the chains suddenly went slack and he fell. The hooks held fast and prevented him from landing. The sudden strain pulled at him and he let out a scream in shock. The process was repeated until Dean lost count. He couldn't die from the blood loss. The hooks would never come loose, and he would never pass out.

_Ahh... Just let it stop!_ "...N-n-no more... p-please..." Now this was torture. But then Dean was aware of something... as he wished for it to stop more than anything, a hook disappeared. _No. Not good._ Dean was suddenly wishing for the hook again, for the pain. If there was pain, he was still human. But the hook never returned and that part of his body became disturbingly numb and that frustrated Dean more. The hook took was gone for good and took a piece of him with it. _No. Stay with it Dean._

The demon raised it's hand and that particular torture stopped.

"Pain a little too much Dean?"

He only glared at the demon. It would take more to break him.

"Get used to the pain down here." The demon grabbed his face. "The pain is all you have. And soon enough..." It waved a hand to wear a hook once was. "Not even that."

"I wouldn't bet on it."

"You will give in. And you will break. You're nothing!"

"I have Sam."

"Aww... you think you're a martyr. Cute. You have no idea what's going on topside. You think you died to save your perfect, moral little brother."

"Shut up." This earned Dean a punch in the gut.

"You listen when I'm talking to you!"

Dean shut his mouth.

"Very good. Now not to give away the ending, but you didn't save Sam... And now you can't kill him. Just like dear old Johnny asked you to the day he died. You royally screwed up Dean. You let Sam down and let him die once, now you just let the entire world down and let him live. You just can't do anything right. And now, the one real job you ever had is gone. You can't save Sam. You can't "watch out for Sammy." No one can. You're not good for anything but being our little toy until you let go. Might as well just admitt it to yourself. What do you have to say to that?"

It smacked Dean across his face hard before he could answer. "And think before you speak this time."

"...nothing..." Dean's voice was a small whisper.

"That's right, you're nothing. And you have nothing to say. I'll leave you to your thoughts."

Suddenly Dean was blind and deaf again. It was harder for him to keep up the mantra that he'd given himself to keep himself going now. He tried not to focus on the numbness and only on the pain. _Feel the pain Dean, feel the pain._

**AN: So what did you think? Any ideas on how you'd like to see Dean tortured are taken into consideration. This is my first go at torturing him and not Sam so I can use the opinions. Good or bad. Reviews rock my salt.**


	7. Chapter 7

**DISCLAIMER: I want but do not have.**

**Thanks to all my reviewers, you rock my salt :D**

**Please be patient with this chapter, all things must start somewhere.**

Sam sat across from Ruby in the hotel lobby. She'd insisted that they not leave this morning so they were eating the free breakfast that came with the room. Sam chose not to eat anything that wasn't pre-packaged or fruit.

He didn't like the seriousness of it all this morning, the way Ruby seemed to be constantly on guard. "So how does this go? You gonna take me to shoot yacks with psycic mind bullets or something?" Sam cracked a smile.

"Yacks, no." Ruby looked up. "But the mind bullets aren't completely out of the question." She smiled. Sam choked, he wasn't serious. She had to be kidding that's just-just...

"You're insane."

"I'm not the one that wanted to go yack hunting."

"So what... what exactly can I do?"

"Nothing right now. You aren't anything near focused. But honestly, I have no idea. You're a mystery Sam."

"Oh."

Ruby stood up. "I'm going back. Finish eating and get back to the room. You're gonna have a busy day."

Sam paused mid-bite into a banana and got up to follow. "What do you mean?"

"We're in a time crunch, every second counts Sam. You start today."

"Ok, then what's first."

"First, we figure out which demons we want to go after."

"Great, I'll just get out Dad's journal and we'll pick a few." Sam mocked.

"No worries Sam. Leave it to me, I've got my own little list." Ruby held up a pad from the motel and opened up the door. "Go get ready for your big day. I've got to go make a few calls." And she was gone leaving Sam alone for the moment.

_You're doing this for Dean, this is going to help him._

After about half an hour Ruby stormed back into the room.

"You ready?"

Sam nodded not knowing what to expect. "So am I bending spoons or giving lotto numbers today?"

"Not funny Sam, I just went to a _hell_ of a lot of trouble for you and you'd better not blow this one so get off your ass and follow me."

Sam followed Ruby to the back of the hotel and she stopped him before rounding a corner.

"Sam, I summoned Seere. He's indifferent towards the conflict between you and Lilith at the moment."

"You summoned a demon?! I thought I had to learn how to use my-"

Ruby held up a hand. "Shut up Sam, he can hear you. Just go in there, don't think about Dean or anything else. Focus on getting him on our side. Nothing else."

"What if I can't?"

"He's a Prince of hell Sam. Don't even think about that possibility." Ruby looked at him darkly.

Sam's eyes went wide as she shoved him forward. "Now go."

"Well, well, well. Sam Winchester. I've heard so much about you but I don't believe we've had the pleasure." A man stood infront of Sam. He would've been mistaken for an angel if his eyes didn't have an eerie glow to them. It was a color Sam couldn't place and the sight left him momentarily speechless.

"My name is Seere. You're lucky you caught me visiting up here. I'm on a vacation of sorts." Seere chuckled.

"Yeah... right." Sam shifted uncomfortably. Seere's gaze never left him and Ruby elbowed Sam.

_For Dean Sam, do this for Dean. You need the army, you need this power._

"If you're looking for news about your brother I'm afraid you've got the wrong demon." He sighed.

Something stirred in Sam. "I'm building an army." The words he thought he'd never say.

"Oh really." Seere was unimpressed.

"I'm going to take Lilith down and I'm looking for any demon that would like to join."

"Who am I joining?"

Sam just looked at Ruby.

"You two? You're kidding."

"No."

"And then what? Become the leader that Azazel promised us? You're nothing. You disappoint me Sam."

Sam's face became darker. "After I take down Lilith, I'm doing whatever the hell I want."

"I'm still not interested. I'll be happy to give you a quick death if you want and a spot in hell next to your brother."

"Join or don't join me." Sam's face twisted at the thought. "But you're not going to kill me."

Ruby tugged on Sam as a que to maybe leave.

"You shouldn't challenge me." Seere made a twisting motion with his hand to snap Sam's neck, yet nothing happened. He then waved his hands forward summoning two lesser demons to attack Sam.

Sam grabbed the first one and through it into a wall as it charged him. He merely looked at the second one and said "Go to hell." and it disappeared.

"...Remarkable..." Seere looked in awe and glanced at the remaining demon cowering near him.

"You can't kill me." Sam stepped forward. He was shocked at the sudden surge of adrenaline and power he felt.

"Indeed... I think I'll stick around and observe at the very least. Summon me whenever you please." Seere then snapped his fingers and disappeared along with the other demon.

Sam stood there in shock. The experience was almost numbing...

"Sam. Sam?"

Sam was pulled out of his thoughts.

"Ruby, I just... I mean I didn't even exorcize..."

"Yeah, I saw. Good job tiger. Could've gone better with Seere, but it looks like we've got him."

"What now?" Sam felt like he could do anything.

Ruby smiled. "There are some demons wandering around town. Nomads. Not very powerful individually, but they have no alliances."

"You think they'll listen."

"If not you can use a little demonstration." Ruby shrugged. "Think of it as your first concert Sam. Like I said, rock star."

Sam was oddly pleased. He knew he shouldn't be. He knew this was wrong. He went over the conversation he'd had with Seere and recalled one detail...

"Ruby. What did Seere mean when he was talking about summoning the wrong demon if I wanted to hear about Dean?"

"Nothing." Ruby snapped a little too fast. "I mean, that's not possible Sam. Besides, you shouldn't be focused on Dean. Seere could see that in the beginning and that's why he said no at first. You were weak. What did you focus on when you sent thing one into a wall and thing two back to hell?"

"I don't know... He just made me angry, mentioning Dean in hell I guess and then I thought about how I needed to live through this. Then the demons charged me and I realized I couldn't stop them on my own and that I needed power..."

"Focus on that Sam. You need that power to stay alive and get an army."

Sam looked away. This was wrong, but it had to be done.

And it did feel a little good to break the rules...

**AN: Dean's turn next chapter. Should I make EVIL!SAM or stick with him being good? VOTE!!**


	8. Chapter 8

**DISCLAIMER: I don't even own a party hat.**

**OK. SO. I scare myself sometimes. Sam's exorcism trick in Lazarus Rising and last chapter are purely coinsidence and I freaked out on the couch as I  
watched it on TV, thus scaring me away from this fic for a bit.  
**  
Dean didn't know how long it was until he was brought back. Apparently, there had been a hand off and he was someone else's problem now. The current demon in charge chose a different way of bringing him back.

"I've always wanted to do that." She said, her face close to Dean.

"And I'll always hate getting violated with demon tongue sweetie." Dean spoke back.

It went in again and kissed him harder. "Just wanted to see if you're as good as they say you are."

"Sorry to disappoint, but I prefer humans."

"You're better." She decided.

The demon moved and went to take the hooks out of Dean. As soon as he was free he collapsed to the ground.

"You're letting me go?"

"Hardly." She put a choke chain around Dean's neck and used it to yank him to his feet. Dean immediately started to claw at it. "I've got other jobs to do, so it's easier for me to take you with me.""What?""I've got other things to do. Now, come on." She started walking.

After what seemed like forever to Dean, he fell. The demon took no notice and dragged him by the chain without a glance. It took great effort but he finally got his footing back.

They passed many demons and Dean almost didn't notice when she stopped short when one crossed her path.

"What are you doing down here?"

The demon glanced at Dean and then back to her.

"Tell me."

The demon tried, but when it spoke nothing came out so it pointed to a confused Dean.

"Something has you gagged."

It nodded.

"Is Seere alright?"

"Yes, I believe so. You know him, he can handle himself."

"I expect a full report later."

"Yes Merra." The demon hung its head and walked off.

"Change of plans. I'm going to keep you close to home. My little corner of hell."Dean found himself in room hours later. He wasn't sure how he got there other than being dragged. God his throat hurt, he wouldn't be able to speak for a while now.

The door opened and the demon that crossed Merra's path before entered.

"You. Get up."

Dean just sat utterly confused.

"I said. Get. Up." Dean flew across the room and hit a wall. He was smart enough to get up this time.

"From the looks of it we won't have to worry about you talking back. But you will do as you're told, you will not make eye contact, and you will not try and escape. Understood?" Silence. "Good."

Then Merra entered the room. Dean looked up to meet her gaze but as he did he found himself kissing the floor seconds later.

"I can read your thoughts Dean. You're here because you're too much in the public eye out there. And what am I going too you today? Nothing, just talk." Merra sat in a chair.

"You see Dean, I know all about you. It's really sad. You're nothing but a hunter. You never meant more than that, not even to your own father. John thought of you as his little insurance policy. Someone to take care of Sam if he got taken out on a hunt, but more importantly he knew you'd finish his little vendeta against Azazel for him. Gee, looks like he was right. Isn't that what happened? Daddy died so you took care of Sam and killed Azazel for him. Then you died. You meant nothing more than that to John."

Dean launched himself at her. He wasn't nothing. His dad loved him, he didn't want this life for him. She was wrong. _Dad needed me and he would've done anything to keep me from this._

Merra kicked him off and held him suspended in mid air. Pain flashed across his face as every part of his body pulled in a different direction like it was trying to rip itself apart. He would've screamed if his throat allowed it.

She left him like that and continued.

"And Sam... Sure he'd never leave you in the middle of a hunt. But when it comes to down time, he's always looking for a way to get away from you. He can't stand the sight of you. He's glad he doesn't have to put up with your sorry ass anymore. Sam can finally hang around someone with a real personality instead of you." She looked at Dean with disgust and spat at him. "Sam keeps _much _better company now. You've been replaced already Dean."

_This isn't true Dean, this is bull and you know it._

"Or is it?" She cocked her head. "But don't worry, we'll make you forget all about it." Merra smiled and traced Dean's jaw line.

She made a motion and Dean was hanging as if invisible ropes were dangling him by his arms from the ceiling. Merra then went to the corner were a bag was waiting. Dean shivered at the thought of what may be coming next.

"I can hear your thoughts so I won't be needing to give you back your voice.

But then again, no one to hear you scream." She smiled wickedly and pulled out a wip that seemed to be made of fire.

CRACK

"You're nothing."

CRACK

"No one gives a shit about you."

CRACK

Dean's very own blood seemed to burn his skin as it flowed. He raised his head screaming silently for someone to help. To save him.

_Too much... No one's coming Dean, it's just you. Pain melted into numbness where blood was burning his skin. No. You want the pain Dean, hold on to it._

Merra just laughed while she listened in on his thoughts.

"Baby, we've got all eternety for pain if that's what you want."

CRACK

And Dean was trapped. Unable to pass out, he only had his mantra to hold onto until she finally approached him and sent him back into the darkness.

**AN: I know it's been a while, hope you like. I could still do with some ways to torture Dean. The vote is still open for whether you want EVIL!SAM or not.  
**


	9. Chapter 9

**Hey guys... Please don't murder me for not updating... I'm sure you wanna read so I'm just gonna... yeah *starts to type frantically*.**

DISCLAIMER: The trunk of my car wasn't big enough for them to fit... I've said too much... *shifty eyes*

UPDATETIMELETSVISITSAMANDRUBYTHISCHAPTER

Sam sat in the motel room with his mind racing and replaying the events of the morning. All he had said was "Go to hell," and it was done. What else could he do? What was the limit? His mind was lost in thought by the time Ruby returned again.

"...Sam, Sam?"

He jumped at her sudden presence. "Ruby."

"You're looking a bit spacey there. Can't afford to be caught off guard."

"I know."

"So I managed to summon the 'locals', you should come with me to talk to them."

"I should exorcize every last one of them."

"No Sam. You need them."

"No, I need Dean."

"Forget about Dean!" Ruby shouted.

Sam stood up quickly.

"I'm sorry, I didn't mean it like that."

"Don't Ruby."

"I just mean that you need your focus on getting the army so you can kill Lilith."

"Lilith... right... and after that Ruby? What do I do when I kill Lilith and still have a demon army?"

"You know the answer to that."

Sam swallowed. "Let's just get this over with."

Ruby led him into town. There was a small bar open, a demon watering hole from the looks of it.

"I've got your back Sam. Seere is watching as well, he'll speak for us if need be."

Sam pushed ahead into the noisy bar. There was absolute silence by the time he was in midst of the bar for all to see.

"Well, all hail the boy king!" One voice dared to laugh and Sam shot an angry look in that direction silencing the voice.

Sam grabbed a shot off of a table and downed it.

"You all know who I am, I'm sure." Sam looked around.

"False messiah! You were meant to lead us!" A woman said as she stood up.

"I never claimed to be your messiah. However, I'm willing to lead you if you join me."

"Join you in what?"

"I'm going to kill Lilith."

Everyone started to murmur in low voices.

"Look at him! He's weak, human." She spat. "He's no match for Lilith. She'll slaughter us. You have nothing Sam Winchester."

"You may know Seere, he's agreed to join my cause along with Ruby."

"That's still nothing compared to what Lilith can do! You were always the weaker Winchester."

"You don't have to join me, but let the others decide for themselves."

"Give us reason. Give us a reason why we shouldn't kill you _Winchester_!" She spat.

"Because you can't." Sam smirked. "And I can send each and everyone of you back into the pit."

"More of us to play with your brother then!" The woman smiled.

Sam was silent.

"That's right, I just climbed out. You should hear him screaming, begging!" She laughed. "I couldn't help but take a shot at him myself on my way out."

"I'll kill you you bitch!" Sam grabbed the woman and started to squeeze her neck with one hand and seemed to hold the demon being expelled with the other. Once the woman went limp Sam held the cloud of smoke for all to see. "No one messes with my brother."

An eerie glow came out of his hands and the swirling mass became smaller until it disappeared completely. Sam was left panting with the effort and focus.

"So who's with us?" Ruby stepped in.

"Step outside and give us some time to decide. Tequila is on the house." The bartender tossed a bottle to Ruby.

"Let's go Sam."

Sam nodded and no sooner after the door to the bar closed, his enormous frame collapsed on Ruby.

"Sam?" She turned him over to find him in a cold sweat and lines of pain across his face. "Shit, Sam this is no time to pass out."  
**  
AN: Of course I had to make it a cliffie :D. Reviews will tell me where I should go with this. Should the bar join Sam? The vote for evil!Sam or good!Sam is still going.**

Next chapter is Dean in hell of course


	10. Chapter 10

**Disclaimer: I own a spectacular sunburn.**

**STORYTIMEYAY**

Merra studied her work carefully. Any lesser man would've lost more of himself in that beating, she had to give Dean that much. The lesser demons couldn't seem to phase him in the time he'd spent in the pit thus far. So she had been sent from, well... not above, to assess which lucky demon should have the privilage of breaking Dean Winchester. Merra remembered his father well, he had escaped unbroken after 120 years of torture.

"Well well well... care to tell me what's going on with this fresh meat?"

Merra was speechless at the new arrival. After all it was a very rare occasion that she met, let alone talked to such a powerful demon.

"Oh come now, I haven't cut out your toungue."

"Sorry sir... how was your visit upstairs?"

"Genocide isn't what it used to be... World War II for instance..." He said as if fondly remembering something.

"I'm sorry to hear that."

"Tell me about this one. I could smell his soul the second I got back."

"Dean Winchester, he's in my custody until I can find someone that can break him."

"Winchester... Winchester... the name sounds familiar..."

"You may have met the boy's father, John Winchester."

"Oh yes... right..."

They both studied Dean before Merra went to heal him so he could be ready for the next round of torture.

She sighed, "There's an aweful lot of demons out there that would give me anything just to get a piece of this one, let alone be the one to break him. I was thinking he would make a nice gift for Seere when he gets back if nothing else..."

"Unless someone with more... expertise would like him of course?" the demon asked.

"Well of course, but you should hear him, he's tough. Strong like his father was. I'm not sure if who would deal with his attitude for an extended period of time."

The demon smiled, "Always liked em' with a little attitude... and there's always room on my rack for a Winchester, Merra."

"There are special... instructions... for this one you could say..."

"I'm well aware, and I think he'd work nicely as part of my plans."

"You want the Winchester then?"

"Yes. In fact I'll take him off of your hands right away."

"Yes sir." Merra began to shackle Dean as if wrapping him up for sale. "How would you like him delivered?"

"You healed him, he can walk."

"Conscious it is then." Merra gave a wicked smile and brought Dean out of his previous state. "You're a lucky man Dean, a special... associate... I suppose you can say has shown an interest in you."

"What are you even talking about?"

"The previous treament wasn't having so much of an affect on your soul so you came into my temporary custody until something could be done."

"You sold me?"

"No. Just found a better place for you." Merra smiled and chills went up Dean's spine, this was bad. "Dean, I want you to meet Alistair, you'll be spending a LOT of time together I'm sure."

"Hello Dean." Alistair smiled. "I knew your Daddy really well, and boy... do I have some big plans for you..."

"You son of a bitch don't talk about my father!" Dean yelled and lunged at Alistair.

"Already angry, that's a good start Dean. I think we should go someplace else to talk though." And with that, Alistair reached into Dean's chest and clutched his heart. "Such potential if you're anything like Daddy was." He then dragged Dean impossibly across hell by his heart to the rack where Alistair kept so many other souls...

**AN: I know it's been a while and I know there isn't a ton of Dean whumpage here, but I can only do so much and some people didn't like the amount of abuse I was putting him through all at once. I've decided to be season 4 friendly with this although it still will be AU. Let me know what you think, the purple button is your friend.**


	11. Chapter 11

**Again, sorry for not updating, but here it is.**

**Disclaimer: I own nothing. If it weren't for my new restaurant job, I wouldn't eat today.**

"Sam? Sam! You _cannot _do this right now!" Ruby was holding Sam up and shaking him.

"Ugghh… Ruby, my head…" Sam was barely keeping himself from passing out.

"I know Sam, you did great in there. But you gotta stay with it or else those demons will come out here and eat us alive… literally…" Ruby grabbed the tequila, "Drink this."

"No… last thing I need is… hangover…" Sam's head felt like it might explode any second. As far as his powers went, the sky wasn't the limit apparently, it was pain tolerance.

"Ok, then-" Ruby heard something and paused before shoving Sam completely upright into the wall and forcing her lips roughly onto his.

Sam was caught off guard and couldn't think in time to shove her off of him. This was so wrong and _disgusting._ He moved his hands to her shoulders to shove her away until he heard a voice…

"I didn't realize that you would be… preoccupied…" Sam could see the bartender with his arms crossed out of the corner of his eye.

Ruby broke away, "You want to tell us something?" She stood close to Sam so she could still hold him up.

"We are going to take the rest of the night to decide. We'll send someone to you in the morning with a decision. In the meantime I'm sure you can find something to do in your room." The demon smiled.

"How do we know you won't attack tonight?" Ruby's eyes were hard.

"You have our word, as long as he doesn't go after us." The demon looked at Sam with fear.

"Fine. You have one night. After that I will come back and believe me, I have no problem with wasting every single one of you." Sam summoned all of his strength for this.

The demon disappeared back into the bar just as Sam began losing strength again and fell forward onto Ruby.

"Shit. Sam get up, I can't carry your dead weight all the way back." Ruby lowered Sam to the ground and tapped his face. Sam was out cold. "You're going to hate me for this…" Ruby took a knife to her wrist and held it to Sam's mouth.

Sam groaned and began to stir, "R'by…?"

"Right here Sam." She hid her wrist before Sam could notice. "We need to go." Ruby reached down to help Sam up.

Sam tasted blood and vaguely remembered passing out. "What happened?"

"I think you over did it a little bit tonight Sam. Let's get you back to the room."

"Yeah… feels that way." Sam held his head. _Hope it was worth it…Sorry Dean…_ Sam thought about the woman he'd just killed. Surely he didn't have to kill the host as well? For some reason though, he couldn't bring himself to care that much as he stepped into the car.

That night Sam dreamed about Dean. He was being tortured endlessly and no matter how Sam called out to him or reached out to him, he couldn't ease his brother's suffering or stop the torture. Parts of him were missing and replaced with smoke.

Sam woke up suddenly only to see Ruby asleep in the next bed. He sighed and looked to his right and Dean was inches from his face with a knife. His eyes were black.

"Dean!" Sam jumped back in the bed.

"That's right Sammy." He held the knife to Sam's face. "And this is what I've become."

"No…"

"Tell me Sam, how long was I gone before you met back up with that _whore_ and let her sleep in my bed?" Dean cut down Sam's right cheek.

"Please… don't…"

"Too late Sam." Dean's voice began to change. "Wake up."

Sam looked confused.

"Wake up SAM!" Dean slapped him and when he turned again to face Dean he saw Ruby.

"Sam! You're having a nightmare!"

He could still feel the phantom cut his brother left and the sting from Ruby's slap.

"Nightmare… Yeah…" Sam said after getting a grip on reality.

**AN: It's been a while so any thoughts would be great. I hope I didn't disappoint this chapter.**


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